potassium dihydrogenphosphate; adogen 464; Fremy’s salt in water 1 h;

1: NaBH4 / tetrahydrofuran; methanol / 4.5 h 2: tosic acid / benzene / 1 h / Heating 3: 80 percent / I2 / benzene / 4 h / Heating 4: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating 5: 71 percent / DDQ / benzene 6: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 7: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: tosic acid / benzene / 1 h / Heating 2: 80 percent / I2 / benzene / 4 h / Heating 3: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating 4: 71 percent / DDQ / benzene 5: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 6: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 80 percent / I2 / benzene / 4 h / Heating 2: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating 3: 71 percent / DDQ / benzene 4: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 5: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 75.3 percent / triphenylcarbinol, CF3COOH / 48 h / Heating 2: NaBH4 / tetrahydrofuran; methanol / 4.5 h 3: tosic acid / benzene / 1 h / Heating 4: 80 percent / I2 / benzene / 4 h / Heating 5: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating 6: 71 percent / DDQ / benzene 7: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 8: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 2: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 71 percent / DDQ / benzene 2: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 3: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 2.97 g / p-toluenesulfonic acid / benzene / 24 h / Heating 2: 71 percent / DDQ / benzene 3: 85 percent / glacial acetic acid, concd. HCl / 24 h / Heating 4: 82 percent / Adogen 464, Fremy's salt, KH2PO4 / H2O / 1 h View Scheme

1: 90 percent / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 2: 70 percent / pyridinium chlorochromate / CH2Cl2 / Ambient temperature 3: 1.) hydrazine, 2.) 40percent NaOH / 1.) diethylene glycol, reflux, 2.) a) 0 deg C, b) 50-60 deg C, c) reflux 4: 80 percent / BBr3 5: 32 percent / Fremy's salt, KH2PO4 / methanol; H2O / 48 h / Ambient temperature View Scheme

1: 1.) hydrazine, 2.) 40percent NaOH / 1.) diethylene glycol, reflux, 2.) a) 0 deg C, b) 50-60 deg C, c) reflux 2: 80 percent / BBr3 3: 32 percent / Fremy's salt, KH2PO4 / methanol; H2O / 48 h / Ambient temperature View Scheme